Water → 1-(4-Bromo-1,3-thiazol-2-YL)piperidine

HRID 347408Notes

Reaction equation

HRID 347408 reaction equation
[N:1]1([C:7]2[S:8][CH:9]=[C:10]([Sn](C)(C)C)[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:16]C1SC=C(Br)N=1.O>N1CCCCC1>[N:1]1([C:7]2[S:8][CH:9]=[C:10]([Br:16])[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 27632972,4-Dibromo-1,3-thiazoleHCID 591182862-Piperidinyl(trimethylstannyl)thiazole

Product 1

HCID 457874991-(4-Bromo-1,3-thiazol-2-YL)piperidineYield 100%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Conditions

Temperature
50 °C

Procedure

Synthesis of 2-Piperidinyl(trimethylstannyl)thiazole 373 as illustrated in FIG. 53. 2,4-Dibromothiazole (358; 1.0 equiv) was dissolved in piperidine (0.5 M) and the reaction was warmed to 50° C. for 8 h, upon which completion of the reaction was indicated by TLC. The mixture was poured into water and extracted with ether (2×). Drying (MgSO4) and evaporation of the solvents gave 2-piperidinyl-4-bromothiazole 372, which was isolated after flash column chromatography (silica gel, 5% EtOAc in hexanes) in 100% yield.

Workup

  1. extractionextracted with ether (2×)
  2. customDrying
  3. custom(MgSO4) and evaporation of the solvents

Sources & evidence

ORD record
ord-63123ab641a34326bbff78639f93cc89
Source dataset
uspto-grants-2007_02
Patent number
US07173137B2

Reaction notes

Loading…